1,6-anhydro-3-deoxy-3-C-vinyl-β-D-mannopyranose | 466646-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-3-deoxy-3-C-vinyl-β-D-mannopyranose
• 英文别名: (1R,2S,3S,4S,5R)-3-vinyl-6,8-dioxabicyclo[3.2.1]octane-2,4-diol；(1R,2S,3S,4S,5R)-3-ethenyl-6,8-dioxabicyclo[3.2.1]octane-2,4-diol
• CAS: 466646-34-4
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: ZUNVEDJYHBOGRD-GWVFRZDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3-deoxy-3-C-vinyl-β-D-mannopyranose 在 盐酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 methyl 2,4-di-O-benzyl-3-deoxy-3-C-vinyl-α-D-mannopyranoside
  参考文献：
  名称：

  Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man and the Disaccharides α-d-Man-(1→3)-d-Man and α-d-Man-(1→6)-d-Man

  摘要：

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.

  DOI：

  10.1021/jo020339z
• 作为产物：
  描述：

  乙烯基溴化镁 、 3,7,9-三氧杂三环[4.2.1.02,4]壬烷-5-醇 以 四氢呋喃 为溶剂， 生成 1,6-anhydro-3-deoxy-3-C-vinyl-β-D-mannopyranose
  参考文献：
  名称：

  A highly convergent synthesis of a branched C-trisaccharide employing a double SmI2-promoted C-glycosylation

  摘要：

  通过 SmI2- 介导的两个甘露糖基吡啶砜单元与单糖二醛的偶联，合成了 α-D-Man-(1→3)-[α-D-Man-(1→6)]- D-Man 的支链 C 三糖类似物。这种方法代表了一种 C-寡糖的高度聚合合成。

  DOI：

  10.1039/b007117j

文献信息

• A highly convergent synthesis of a branched C-trisaccharide employing a double SmI2-promoted C-glycosylation
  作者：Lise Munch Mikkelsen、Sussie Lerche Krintel、Troels Skrydstrup、Jesús Jiménez-Barbero

  DOI：10.1039/b007117j

  日期：——

  The branched C-trisaccharide analogue of α-D-Man-(1→3)-[α-D-Man-(1→6)]- D-Man has been synthesised by the SmI2-mediated coupling of two mannosyl pyridyl sulfone units to a monosaccharide dialdehyde. This approach represents a highly convergent synthesis of a C-oligosaccharide.

  通过 SmI2- 介导的两个甘露糖基吡啶砜单元与单糖二醛的偶联，合成了 α-D-Man-(1→3)-[α-D-Man-(1→6)]- D-Man 的支链 C 三糖类似物。这种方法代表了一种 C-寡糖的高度聚合合成。
• MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20140107049A1

  公开（公告）日：2014-04-17

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. The invention also provides processes for making the compounds of the invention. The compounds of the present invention are represented by the following structure of Formula A: wherein the variables are as described herein.

  本发明涉及用于治疗或预防细菌感染的化合物。本发明还提供含有该化合物的药学上可接受的组合物以及使用该组合物治疗细菌感染的方法。本发明还提供制备本发明化合物的方法。本发明的化合物由以下A式结构表示：其中变量如本文所述。
• Application of the Anomeric Samarium Route for the Convergent Synthesis of the <i>C</i>-Linked Trisaccharide α-<scp>d</scp>-Man-(1→3)-[α-<scp>d</scp>-Man-(1→6)]-<scp>d</scp>-Man and the Disaccharides α-<scp>d</scp>-Man-(1→3)-<scp>d</scp>-Man and α-<scp>d</scp>-Man-(1→6)-<scp>d</scp>-Man
  作者：Lise Munch Mikkelsen、Sussie Lerche Krintel、Jesús Jiménez-Barbero、Troels Skrydstrup

  DOI：10.1021/jo020339z

  日期：2002.9.1

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.